Mothproofing agent



Patented Apr. 17, 1934 PATENT car es uo'rnraoor'ma AGENT v Hermann Stiitter and Theodor Hermann, Leverkusen-I. G. Werk,

Germany Fubenindustrie Aktlengesellschal' on-the-Main,

, asaignors to I. G.

t, Frankfortntnmving. Application June 20, 1932, Serial No. 618,341. "In Germany September 1c, 1931 7 The-present invention relates to a process 01' protecting materials against attack by textile pests and tothe'compositions employed therein.

p In the'copend'ing U." 5. application Ser. No.

371,950, filed 14, 1929, agents are described for rendering, wool, fur, hair, feathers and the like proof against attack by moths.

These mothiprooflng agents generally consist of arylsulio'nic acid amides of the general 10 formula: I

16 wherein It stands for an aromatic nucleus, R1 and R2 stand. for hydrogen or a radical selected from the group consisting of alkyl radicals, aryl and aralkyl, and wherein all nuclei may further contain a substituent selected from the group consisting of hydroxyhalogen-, alkyl-, aryl-, alkylacidy1amino-, arylacidylamino-,. sulionic acidand carboxylic acid groups.

These compounds are highly active moth proofing agents, and, furthermore, excellently protectl wool, feathers, hair and the like also against the attack by other important textile pests, such as anthrenus Iasciatus, attagenus japonicus or attagenus piceus ol. Thereby they difier from other moth proofing agents, such as chlorinated naphthalenes, cinchona alkaloids and esters of phosphoric 'acid which are effective against moths, but ineffective against these textile pests.

amides, however, was limited hitherto, as they are not sufliciently soluble in benzine, carbon tetrachloride or trichlorethylene which are being principally-used in dry cleaning, and therefore m could not be used for such finished articles, for instance, clothes, iurs, upholstered furniture, museum specimens liable to attack by moths oi! felt in pianos, as are not suitable for a treatment with a water solution. I

We have now found that arylsulfonic acid amides of the above formula which are tree from tree sulionicor carboxylic :acid groups, when mixed withlphosphoric acid esters of the general formula:

, wherein R1, Ra, Ra means similar or dissimilar radicals selected from the group consisting of amide, such as the The application of these arylsultonic acid allryl, aryl and aralkyl radicals which may contain substituents selectedfrom the group consisting of halogen (Cl, Br.) and alkoxy (QCHa, OCaHs), are very easily soluble in benzine, carbon tetrachloride, trichlorethylene and other organic solvents. Therefore, such mixtures can be used in the customary dry cleaning solvents for protecting the articles mentioned above against attack by moths or other textile pests.

' These new mixtures generally represent colorless or faintly colored oils. The quantity of the active components to be applied for protecting materials against textilepests may vary within wide limits. For the mixture we generally use about two parts by weight of phosphoric acid ester, such as'the diethylbutylglycolphosphate, and one part by weight of an arylsulfonic acid 3,4-dichlorobenzenesulfomethylamide. The new compositions may be applied in any of the known manners. Thus, for example, the oilean be dissolved in benzine and sprayed on the materials to be protected or the same can be soaked with the solution or otherwise moistened therewith.

The following examples will illustrate our inso yention, but without limiting it thereto. The

parts are by weight.

Example 1.-Wool, feathers or hair are. treat ed in a benzine solution of the mixture containing 2 parts of 3,4-dichlorobenzene-sulfomethylamide of the formula H O1G0:.N/

OlEh and 3 parts of diethylbutylglycolphosphate oi the formula:

CIHIO CIHIOP=O treated in a benzine solution containing a mixture of 1 part of 3,4-dichlorobenzenesulfophenylamide of the formula:

, cPQosNH-O (melting point 82' C.)

in 1 part of triethylphosphate and 0.5 part of diethylbutylglycolphosphate.

Example 4.The goods are treated with a trichloroethylene solution of 1 part of 3,4-dichlorobenzenesulfo 2 methylbenzeneamide (melting point 110 C.) in 0.5 part of triethylphosphate and 1 part of diethylbutylglycolphosphate.

Example 5.The goods are treated with a carbon tetrachloride solution of 1 part of 3.4-dichlorobenzenesulfamide (melting point 136 C.) and 2 parts of triethylphosphate.

Example 6.The protecting solution consists of trichlorethylene containing a mixture of 1 part of dichlorobenzenesulfodimethylamide (melting point 128 C.) and 1.5 parts of triethylphosphate.

Example 7.-The protecting solution consists of benzine containing a mixture of 1 part of 3.4 dichlorobenzenesulfodiethylamide (melting point 58 C.) and 1.5 parts of tri-isoamylphosphate.

Example 8.The protecting solution consists of benzine containing a mixture of 1 part of 3,4 dichlorobenzenesulfodibutylamide (melting point 56 C.) and 1.5 parts of dibutylamylphosphate.

Example 9.-The protecting solution consists of carbon tetrachloride containing a mixture of 1 part of 3,4 dichlorobenzenesulfobutylamide (melting point 77 C.) and 1.5 parts of tricresylphosphate.

Example 10.-The protecting solution consists of trichlorethylene containing a mixture of 1 part of 3,4-dichlorobenzenesul1'ostearic amide of the formula:

CQOLNBLOOOMBI in 1.5 parts of diethylbutylglycolphosphate.

Example 11 .--The protecting solution consists of perchlorethylene of the formula:

(boiling point 121 C.)

containing a mixture of 1 part of 3,4-dichlorobenzenesulfoleic amide of the formula:

* Ol-QGO NHDOOuHa and 1 part of diethylglycolphosphate and 1 part of tributylphosphate. Goods treated with the wherein R stands for an aromatic nucleus, and R1 and R2 stand for hydrogen or a radical selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of hydroxy, halogen, acidyl and alkylor arylacidylamino groups-but are free from free -sul fonic and carboxylic acid groups, and a phosphoric acid ester of the general formula:

wherein R1, R2 and R: mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.

' 2. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:

RBOLN wherein R1, R2 and R: mean similar or dissimilar radicals selected from the group consisting of alkyl, arallgyl and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.

3. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:

wherein one X stands for a halogen atom, and the other X stands for hydrogen or a halogen atom; R1 and R2 stand for hydrogen or a substituent selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of hydroxy, halogen, alkyl, aryl, acidyl and alkylor aryl-acidylamino groups, but are free from free sulfonic and carboxylic acid groups, and a phosphoric acid ester of the general formula:

wherein R1, R2 and R3 mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl, and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic sol-' vents and generally representing colorless or faintly colored oils.

4. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:

wherein one X stands for a halogen atom, and the other X stands for hydrogen or a halogen atom; R1 stands for hydrogen or a substituent selected from the group consisting of alkyl, aralkyl and aryl radicals, and a phosphoric acid ester of the general formula:

wherein R1, R2 and R: mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl and aryl radicals which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.

5. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the'general formula:

wherein R1 stands for CH3, C2115 or C4119, and a phosphoric acid ester of the general formula:

wherein R1, R2 and Rs mean similar or dissimilar radicals selected from the group consisting of CH3, CzHs, CsH'z, CiHs, C4H9.OCH2.CH2, Col-I5, CH3.C6H4 and CLCSH4, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.

. 6. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide 90 of the general formula:

H (Cra OHz and a phosphoric ester of the formula:

(hHIO C2HuO-P=O oim-o-mc-cmo said composition being soluble in organic solvents and representing a colorless or faintly colored oil.

'7. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:.'

and a phosphoric acid ester of the formula:

CIHIO CaHlO said composition being soluble in organic solvents and representing a colorless or faintly'colored oil. I

8. A textile pest-proofing composition com prising a mixture of an arylsulfonic acid amide of the general formula:

p H CI SOLN/ and a phosphoric acid ester of the formula: 13o

CIHOO C4H|O-P==O said composition being soluble in organic solvents and representing a colorless or faintly colored oil.

HERMANN STOTTER.

THEODOR HERMANN. 

